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API'KNDIX                                        245

The fact that they arc eminently imsaturated compounds is
evidenced by their general behaviour towards a great variety
of reagents.

1.   On reduction they give the primary amine (Mendius),

CM1..CN   1  2llo- CIi:!CII.,NIL,

2.   With HC1, ITIir, and HI they form imidohalides (Wallach),

CllnCN  I  HC1 -Cll,,


3. With alcohol and II Cl they form the hydrochloride of the
imidoethers, from which caustic alkali liberates the base

CII..CN i c,Mnon -i i in -cM.x

Cll;,C      ;(;1Ip      I   NaOIl ..... (:il:,CUr-f  NaCH   II,O.

These imidoethers unite with ammonia and amines and form
the amidines,


4. The latter are also formed by the direct action of ammonia
on the cyanide,

5. I lydroxylamtnc unites with the cyanides, forming armd-
ni.,.CN  I- NlUm - Cn:{.t;<X^jjH.
0. With H.,S the; thiamides are formed,
ni.,.cN i u,,s - cn:,.cs.NH2.
Methylamine Hydrochloride.- -This reaction, which
yields the primary amine, is applicable, not only to the aliphatic,
but also to the aromatic amides. The formation of anthranilic acid
from phthalimide is a process of technical importance. By the